By Jennifer Stevens

Surrounded by the Gulf of America, the Atlantic Ocean, and the Florida Straits, Florida is one of the top sailing destinations in the world.

From the famous regattas in Miami to the myriad of sunset sailing cruises on Florida’s ocean waters, there are dozens of opportunities to experience sailing culture in Florida.

Whether you’re looking to sail your own boat, rent one, or hire a charter, here’s everything you need to know about sailing across Florida’s eight regions.

Northwest Florida
Charters and Rentals in the Emerald Coast and Pensacola Bay

Sailors are drawn to Northwest Florida for the diversity of sailing conditions, the emerald green waters and the plethora of white-sand beaches and islands. Some of the top sailing destinations in this area are Destin, Choctawhatchee Bay, and Pensacola—all offering different types of sailing experiences.

The boating scene in Destin is well-established, and the city boasts a thriving sailing community. Located along the Gulf of America, the Destin area offers sailors beautiful clear waters and award-winning beaches, with a mix of calm and more challenging open Gulf areas. There are lots of sailing charters to choose from, but some of the most renowned are Southern Country Sailing, East Pass Sailing Company, Smile-n-Wave Sailing Adventures, Vitamin Sea Sailing Charters, and Sailing Moby’s sailing cruises and tours. These companies provide private and luxury sailing charters on the Gulf of America with options to visit Crab Island and to go swimming and snorkeling. Closeby in Niceville, MidBay Sailing takes guests out on the tranquil Choctawhatchee Bay, where there’s nothing to do but take in the scenic surroundings and spot dolphins.

 

About an hour west of Destin is Pensacola: a town famous for its sugar-sand beaches, nature preserves, turquoise waters, and of course, sailing. Pensacola Bay, Perdido Bay, and Santa Rosa Sound are all calm bodies of water where you can find several outfitters offering sailing packages. Jolly Sailing and Peace Sailing are both popular companies that lead sunset sailing tours. Peace Sailing also hosts private 8-hour sailing charters to the historic Fort McCree: an old military fort located on a beautiful small island on the western side of Pensacola Bay. For those with sailing experience who want to rent their own sailboat, Key Sailing has 14-foot Hobie Waves and 16-foot Hobie Getaways for rent, which hold 2-3 people and 3-6 people, respectively. Additionally, there are quite a few rental (and charter) options on getmyboat.com.

North Central Florida
For Experienced Sailors with their Own Boats

While not necessarily a sailing destination, Florida’s Big Bend coastline does offer a unique boating experience for people who already have a sailboat. Known as Florida’s “Forgotten Coast,” the coastal area in North Central Florida is like stepping back in time—making it the perfect place for experienced sailors who are looking for peace and nature.

Part of the famous “Great Loop,” the stretch from Carrabelle to Tarpon Springs is often described as a difficult sail, with shallow waters and sand bars. Those who have smaller sailboats should be fine, and can stay somewhat closer to shore, exploring the idyllic coastal towns of Steinhatchee and Cedar Key. In both towns, you can rent slips from the respective marinas (The Sea Hag in Steinhatchee and CK Marina in Cedar Key).

The waters around Cedar Key are part of a network of marshes, shallow tidal areas and small islands—making it an area that is both extremely scenic but also potentially dangerous if not navigated properly. Use your judgment when deciding to sail Florida’s Big Bend, and contact the marinas in advance, as they suffered hurricane damage in 2024.

Sailboats along the Fernandina Beach waterfront.

 Climb aboard a sailboat along the Fernandina Beach waterfront for the best view of the sunset.
-Amelia Island TDC

 

Northeast Florida
Sailing Past Historical Backdrops and Barrier Islands

From the Intracoastal Waterway in St. Augustine to the rivers and Atlantic Ocean in Amelia Island and Jacksonville, Florida’s Northeast region has a diverse array of sailing options. These cities have well-maintained marinas and plenty of charter companies, making them perfect destinations for sailing enthusiasts.

St. Augustine, the nation’s oldest city, offers a historic backdrop for sailing expeditions on the Intracoastal Waterway. St. Augustine Sailing allows visitors to charter their own private sailing yacht as well as join shared day and sunset charters on the Matanzas River. The company also provides sailing lessons and a two-hour “intro to sailing” course. Just outside the city, on Anastasia Island along the Atlantic Ocean, experienced sailors can rent small Aqua Finn sailboats through Anastasia Watersports. Here, guests can sail down Salt Run, a scenic tidal estuary protected by dunes, full of wildlife. 

About 60 miles north of St. Augustine is the charming Amelia Island: a barrier island known for its stunning beaches and laid-back vibe. Sailing enthusiasts will love the easy access to the Intracoastal Waterway and the Atlantic Ocean, as well as the calm waters and beautiful scenery. For those wanting a luxurious sail, Follow That Dream Sailing offers private charters on its 41-foot catamaran around Amelia and Cumberland Islands as well as Fernandina Beach. There’s also the option to explore the area further with overnight and multi-day cruise packages. Additionally, Windward Sailing provides not only private charters but has the option for qualified captains to rent a catamaran bareboat charter and also to take sailing courses.

And finally, you can also find sailing opportunities in Jacksonville: a city known for its extensive coastline, rich cultural scene, and water activities. You can enjoy sunset and day sails on the St. Johns River with Now and Zen Sailing Charters on their 42-foot Manta catamaran, or charter Nepenthe Charter Sailing’s 64-foot Sailing Ketch for a day or even an overnight sail.

Central Florida
Inland Sailing on Freshwater Lakes

While Central Florida may not seem like much of a sailing destination, the Orlando area actually has plenty of large, freshwater lakes, which are perfect for calm sails in unique surroundings. In particular, Lake Fairview, Lake Monroe, and Lake Baldwin are popular spots for local sailing enthusiasts.

Just north of Downtown Orlando is Lake Fairview: a 405-acre body of water that has its own harbor. At Lake Fairview Marina, experienced sailors can rent their own catamaran or hire 16 or 23-foot Com-Pac sailing yachts for up to four hours. For those who aren’t trained sailors, Sailing Orlando offers two-hour private day or sunset tours, as well as three-day courses to obtain an American Sailing Association 101 Certification.

Nearby Sanford is home to one of Central Florida’s largest lakes: Lake Monroe. Part of the St. Johns River system, the lake is home to several marinas, as well as the private Lake Monroe Sailing Association and U-SAIL sailing school and boat club. The lake is not only popular among sailors, but also birdwatchers, and anglers looking to catch largemouth bass (who hold a freshwater fishing license).

Another Central Florida lake popular among the local sailing community is Lake Baldwin in charming Winter Park. Here, The Sailing Club hosts regular events like races, and offers small sailboat certifications for students older than 16, as well as access to 12 dinghy sailboats for its members.

Central East Florida
Atlantic Waves and Calm River Sails

From Florida’s Space Coast down to the Treasure Coast, the state’s Central East region is a sailing paradise. There are opportunities to sail calm lagoons, protected rivers, and enjoy offshore adventures on the Atlantic Ocean.

About an hour northeast of Orlando is the lively beach town of Daytona, popular among families, partiers, and those looking for chartered sailing tours. Howling Owl Sailing offers public and private charters on the Halifax River and around Daytona Beach on their 36-foot catamaran. Halifax River in particular, which is part of Florida's Intracoastal Waterway, is a scenic estuarine river, home to the Halifax River Yacht Club and Halifax Youth Sailing school—popular among sailors who want a calm, coastal sailing experience.

Further south is Florida’s premier surfing destination: Cocoa Beach. While it’s true the waves are consistent in this area, they are generally mild to moderate—making perfect conditions for those who prefer the thrill of sailing on ocean swells. There’s also the option of sailing on the Banana River Lagoon or the Indian River, located just 15 minutes away on Merritt Island. For sailing charters, Cocoa Beach Catamaran is recommended for dolphin cruises, sunset sails and private excursions, and Freedom Sailing Adventures offers a great “old fashioned” sailing experience. 

 Known as the “Sailfish Capital of the World,” Stuart is a small, picturesque fishing town with access to both the Atlantic Ocean and the 35-mile St. Lucie River. Stuart Sailing takes guests out on private day charters, sunset sails, and overnight trips. Their Leopard 40 catamaran has four private cabins and two bathrooms, and charters come with a two-person crew. Another popular charter company out of Stuart is Treasure Coast Sailing Adventures, which operates public, private, and sunset sails along the river. And just a 10-minute drive away in Jensen Beach is the US Sailing Center, which is a sailing school and regatta host that offers private skipper sails Wednedsays through Sundays.

Central West Florida
White Sand Beaches and Preserved Islands

No matter where you go along Tampa Bay, you’re sure to see sailboats dotting the Gulf waters. All the way from Dunedin in Tampa Bay’s north to St. Petersburg in its south, there’s no shortage of beautiful beaches and state parks to explore via sailing charter.

The quaint Gulf town of Dunedin is a great base for sailing enthusiasts wanting to sail the St. Joseph Sound or explore the pristine state parks of Caladesi Island, Honeymoon Island, and Anclote Key. The companies Wind Star Charters and Dunedin Sailing Charters make it easy to visit all of these must-see destinations in one eight-hour sail day, and their 41-foot Morgan Out Island Ketches comfortably fit up to six people.

About seven miles south of Dunedin is another popular sailing base: Clearwater Beach. Schooner Clearwater offers two-hour public day and sunset sails on its 52-foot staysail schooner, for the chance to see dolphins and also the white-sand beaches of Clearwater from the Gulf of America. For experienced sailors, there’s also the opportunity to rent a variety of sailing vessels (14-foot Hobie catamarans, 16-foot Hobie Getaway catamarans, Laser single-handed dinghies, and windsurfers) from the Clearwater Community Sailing Center. The center also offers sailing lessons and hosts multiple regattas throughout the year.

Another Tampa Bay hot spot for sailing is St. Petersburg. The city’s waterfront downtown area and its beaches are popular launching points for sailboats, with both charter and rental options. From St. Pete’s downtown Harborage Marina, St. Pete Sailing Charters takes guests out on its Morgan 44 Center Cockpit monohull sailing yacht for day and sunset sails, and specializes in special events like proposals and even small weddings. Tampa Bay Sunset Sail is also based in downtown St. Pete, taking guests around the city’s beautiful waterfront on a brand new 47-foot luxury sailboat. Outside of the city, Suncoast Sailing’s iconic schooners cruise the calm waters of Boca Ciega Bay, the Gulf of America, and the historic John’s Pass, along St. Petersburg’s world-renowned white-sand beaches.

Sailing & Waterfront Dining in Key West

Southwest Florida
Explore Hundreds of Islands by Sailboat

From the tranquil waters of Charlotte Harbor to the vibrant coastal charms of Marco Island and the Fort Myers area, Southwest Florida is a region every sailing aficionado should visit.

Charlotte Harbor, located between Sarasota and Cape Coral, is renowned for its calm, protected waters, steady winds, and scenic views of mangrove forests and idyllic waterside towns. The harbor is part of the Charlotte Harbor Estuary, which encompasses 270-square-miles of open water, preserved state parks, and aquatic preserves. Florida Sailboat Charter is one of Charlotte Harbor’s premier sailing companies, offering public and private sailing charters as well as a three-day tour of the area’s barrier islands, Cayo Costa, Cabbage Key, and Captiva.

Further south is Marco Island: the only developed island of Florida’s famous Ten Thousand Islands. A chain of mangrove-covered islands and keys, this other-worldy destination is only accessible by boat, and Easy Breezy Charters sails there on its 42-foot catamaran. Another Marco Island charter company is Cool Beans Cruises, who hosts day tours, champagne sunset sails, and private charter packages around the area, often stopping at barrier islands to swim and collect shells.

For serious shellers, the remote islands of Sanibel and Captiva are world-famous; and Copacetic Sailing takes charter guests out to these shell-lined shores as part of its day sails. The company is based in Fort Myers, and has charter options to sail the Caloosahatchee River into the Gulf of America, exploring the area’s gorgeous aquatic preserves and white-sand beaches.

Miami: The Sailing Capital of the South

Southeast Florida
The Sailing Capital of the State

This region of Florida is definitely the most popular for sailing, as Fort Lauderdale is often lauded as the “Venice of America,” and Miami the “Sailing Capital of Florida.” And with its world-class sailing conditions and laid-back tropical vibe, sailing the Florida Keys is often a big bucket list item for sea voyagers.

Fort Lauderdale, with its extensive waterways and easy access to the Atlantic Ocean, is a really fun sailing destination. Starting in downtown Fort Lauderdale, many of the charters first take you down the Intracoastal Waterway, past the city’s vibrant waterfront area and “Millionaire’s Row” of homes before reaching the ocean. Both Tropical Sailing and Sailing Daffy take this route, and offer private and public charters.

Sailing in Biscayne Bay, located just off the coast of Miami, is a great experience—with calm, turquoise waters, panoramic views of the Miami skyline, and lush mangrove shorelines. Sailing Adventures Miami has a variety of options, from two-hour charters around the bay to a full day of sailing and snorkeling, and leaves from Miami’s prime sailing neighborhood of Coconut Grove. In the same neighborhood, Destino Charters has similar offerings, with the option to book overnight charters from one night all the way to eight nights. The longer overnight adventures sail all the way to Key West and back, with snorkeling, shipwrecks, and dive bars on the itinerary. Another option is to book a sailboat direct from the owner on Sailo—either bareboat or with a captain.

Whether you’re sailing to the Florida Keys from Miami, or hiring a charter from Key West (the most popular place for sailing charters), you’ll find plenty of well-reviewed companies to take you out on the water. Argo Navis is a luxury catamaran outfitter with day sail, sunset sail, and private sailing charter packages available. Schooner Appledore has similar offerings, but on historic wooden schooners; and the Tall Ship Jolly II Rover allows guests to join public day and sunset cruises on the area’s most photographed sailboat. Some of Key West’s favorite private charter companies include Catamaran Echo, Danger Charters, and Sunset Sail Key West.

Keep in Mind…

Places to Remember